This article explores John Dewey's Depression-era analysis of "liberalism" in an effort to clarify our own neoliberal moment. As Dewey argues, liberalism is a term used in the 1930s to signify diverse and often contradictory meanings. It variously refers to a minimalist state aimed at unbinding markets (laissez-faire liberalism) or an activist state charged with providing social welfare (what Dewey described as "humane liberalism"). Finding limitations in these visions of liberalism, Dewey calls for a "radical" liberalism that would socialise the economy, challenge the corrupting power of privileged elites, and embrace experimentalism and mass participation in social planning and decision-making. The article draws on Dewey's analysis of different liberalisms to make sense of contemporary political and educational debates that have been profoundly shaped by the growing prominence of neoliberalism in recent decades. It sheds light on why particular educational issues have emerged as central sites of contest while others receive little or no attention and hints at possibilities for social reconstruction.